1-tert-butyl-5-(2,2,2-trifluoroethylsulfonyl)-1H-tetrazole | 1465812-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-tert-butyl-5-(2,2,2-trifluoroethylsulfonyl)-1H-tetrazole
• 英文别名: 1-tert-butyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone
• CAS: 1465812-80-9
• 化学式: C₇H₁₁F₃N₄O₂S
• 分子量: 272.251
• InChiKey: VODHEQRZPYCFID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-tert-butyl-5-(2,2,2-trifluoroethylsulfonyl)-1H-tetrazole 、 2-萘甲醛 在 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  Julia–Kocienski approach to trifluoromethyl-substituted alkenes

  摘要：

  A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.069
• 作为产物：
  描述：

  1-tert-butyl-5-(2,2,2-trifluoroethylthio)-1H-tetrazole 在 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 96.0h， 以1.12 g的产率得到1-tert-butyl-5-(2,2,2-trifluoroethylsulfonyl)-1H-tetrazole
  参考文献：
  名称：

  Julia–Kocienski approach to trifluoromethyl-substituted alkenes

  摘要：

  A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.069